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Drabowsky was Jewish.[1][2] He was born in Ozanna, a village in southern Poland.[3] He came to the U.S. with his mother in 1938, and his father joined them a year later.[4] They lived in Wilson, Connecticut, just north of Hartford, where he went to the Loomis Chaffee School.

Drabowsky attended Trinity College in Hartford, Connecticut, playing on their varsity baseball team. He played summers in Canada, in the Halifax and District League, for Truro. He pitched a no-hitter for Trinity in which he struck out 16, and shortly thereafter accepted a $75,000 ($651,000 today) bonus to sign with the Cubs.[5]

In 1957 Drabowsky met his wife, Elisabeth Johns, a flight attendant for United Airlines, while traveling with his teammates. They were married in 1958 and welcomed three daughters into the world. Deborah Lynn (1959), Myra Beth (1965) and Laura Anne (1972). Elisabeth was always the one true love of his life, and though they had gone separate ways, they were each other's soul mates and had reconnected before his passing in 2006.

Now pitching out of the bullpen, Drabowsky won six with no losses and seven saves, and struck out 96 in 98 innings pitched. In the opening game of the 1966 World Series against the Los Angeles Dodgers, Drabowsky entered the game in the third inning with one out and the bases loaded. After striking out the first batter, he walked Jim Gilliam to force in Lou Johnson for a run to cut Baltimore's lead to 4–2. That would be the last run the Dodgers scored in the entire series, however, as the Orioles would sweep the Dodgers 4–0, their next three wins coming on shutouts from Jim Palmer, Wally Bunker and the starter Drabowsky had relieved in Game 1, Dave McNally. He set a still-standing one-game World Series record for relievers by striking out 11 batters, including tying Hod Eller's 47-year record of six consecutive strikeouts in the 1919 World Series.

Over the next two seasons, Drabowsky continued to perform excellently in relief. In 1967, he posted a 1.60 earned run average striking out 96 in 952⁄3 innings pitched, and in 1968 he posted a 1.91 ERA. After the 1968 season, he was selected by the Royals in the expansion draft; he led all relief pitchers in 1969 with 11 victories (including the first-ever game in Royals history, on April 8 against the Minnesota Twins) and also saved 11 games. Drabowsky returned to the Orioles in 1970 where he won a second World Series title against the Cincinnati Reds.

Drabowsky was traded to St. Louis after the 1970 season and pitched for both the Cardinals through the middle of the 1971 season. Then he finished his major league career with the Chicago White Sox in 1972.

Even though he was signed as a Bonus Baby, Drabowsky spent parts of 4 seasons in the minors in the early 1960s where he won 27 games and lost 9.

In 17 seasons Drabowsky won 88 games, lost 105, saved 55, struck out 1162 and walked 702 in 1641 innings pitched with a 3.71 ERA.

Drabowsky served as a Chicago White Sox coach in 1986. In 1987, he returned to Poland as a baseball ambassador and helped his birth nation form its first team for Olympic competition. In 1989 he was the pitching coach of the Vancouver PCL team.[7] He later became a coach again with the 1994 Cubs.

Drabowsky was well known as a flake whose jokes involved, among other things, being rolled to first base in a wheelchair after being hit on the foot by a pitch while with the Cubs. (Teammate Dick Drott obtained the wheelchair and pushed Drabowsky to first—and was ejected from the game.[8]) One of his specialties was the Hot foot; he even victimized Commissioner Bowie Kuhn during the Orioles' 1970 World Series celebration. After retiring, he once called the bullpen phone and imitated Oriole manager Earl Weaver to get a reliever working. Weaver was shocked to see a reliever warming up in the pen and called his bullpen coach to find out what was going on. In the Jim Bouton book "Ball Four", one of Drabowsky's teammates claimed that Drabowsky got sick on a team flight and "puked up a panty girdle."

In Chicago columnist Mike Royko's annual Cubs quiz, April 11, 1968 (One More Time: The Best of Mike Royko, University of Chicago, 1999, p. 29–31), he stated that Drabowsky "is still considered the best pitcher that Ozanna, Poland, ever produced." Drabowsky was inducted into the National Polish-American Sports Hall of Fame in 1999.[1]

While with the Cubs, Drabowsky gave up Stan Musial's 3,000th career base hit in 1958. He was also the losing pitcher, as a Kansas City Athletic in 1963, in Early Wynn's 300th career victory.